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Enantioselective Catalysis in Fluorinated Media – Synthesis and Properties of Chiral Perfluoroalkylated (Salen)manganese Complexes
Author(s) -
Pozzi Gianluca,
Cavazzini Marco,
Cinato Flavio,
Montanari Fernando,
Quici Silvio
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199908)1999:8<1947::aid-ejoc1947>3.0.co;2-k
Subject(s) - chemistry , enantioselective synthesis , catalysis , indene , manganese , enantiomer , organic chemistry , oxide , organic synthesis , metal salen complexes , combinatorial chemistry
Chiral (salen)manganese complexes, which are selectively soluble in perfluorocarbons, were synthesized and tested as epoxidation catalysts in fluorous‐organic two‐phase systems. The immiscibility of the perfluorocarbons with regular organic solvents allowed a quick and effective separation of the catalyst from the products. These unprecedented perfluoroalkylated salen complexes were found to be efficient and chemoselective catalysts in the presence of several oxygen donors, but enantioselectivities were generally poor. An interesting exception to this behaviour was observed in the asymmetric epoxidation of indene that provides indene oxide with 70–92% enantiomeric excess.